EP2367682B1 - Beschichtungszusammensetzungen und beschichtete substrate für fertigungsartikel, die in kontakt mit flächen des menschlichen körpers verwendet werden - Google Patents

Beschichtungszusammensetzungen und beschichtete substrate für fertigungsartikel, die in kontakt mit flächen des menschlichen körpers verwendet werden Download PDF

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Publication number
EP2367682B1
EP2367682B1 EP09828206.4A EP09828206A EP2367682B1 EP 2367682 B1 EP2367682 B1 EP 2367682B1 EP 09828206 A EP09828206 A EP 09828206A EP 2367682 B1 EP2367682 B1 EP 2367682B1
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Prior art keywords
composition
temperature
coating
aliphatic alcohol
substrate
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EP09828206.4A
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English (en)
French (fr)
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EP2367682A1 (de
EP2367682A4 (de
Inventor
Linda M. Pierson
Susan K. Brown-Skrobot
Ching-Yun M. Yang
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Johnson and Johnson Consumer Inc
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McNeil PPC Inc
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Priority to PL09828206T priority Critical patent/PL2367682T3/pl
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Publication of EP2367682A4 publication Critical patent/EP2367682A4/de
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0034Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • A61K9/0036Devices retained in the vagina or cervix for a prolonged period, e.g. intravaginal rings, medicated tampons, medicated diaphragms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D191/00Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C09D191/06Waxes

Definitions

  • the present invention relates to coating compositions for flexible, sheet-like substrates, coated flexible, sheet-like substrates for articles of manufacture used in contact with human body surfaces, and a process for adding waxy compositions to flexible, sheet-like substrates.
  • the present invention is particularly useful for coating compositions for flexible, sheet-like substrates, coated flexible, sheet-like substrates used in the manufacture of disposable absorbent articles, specifically suited for coated flexible, sheet-like substrates used in the manufacture of tampons.
  • Disposable absorbent articles can be used as vehicles for topical delivery to the vaginal canal, perineum, and related areas, as well as for treatment sites for the discharged fluids to come in contact with the waxy compositions, as they are captured by the product.
  • Duchane, US Pat. No. 3,796,219 discloses a water-soluble, thermoplastic compound for hygienic and medical applications, such as for use as an insertion aid coating for tampons and as the matrix structure for suppositories.
  • the coating is stable in temperatures up to 65° C, and it provides lubricity at temperatures below 65° C when exposed to shear forces, as those present during insertion of the tampon.
  • Duchane discloses the use of two olefinic diols, polyethylene glycol and propylene glycol in combination with hydroxypropyl cellulose (HPC) having a molecular weight of approximately 75,000. The resulting composition is stable at temperatures up to 65° C. Von Bittera et al., US Pat.
  • No. 4,582,717 discloses a process for producing vaginal tampons containing a pharmaceutical active compound. The process involves preparing a material containing the active compound and additional formulation auxiliaries, heating the material to a temperature in excess of 40° C, cooling the melt to 40° C, and then injecting the cooled material into pre-warmed tampons.
  • One of the formulation auxiliaries disclosed in von Bittera is polyethylene glycol (PEG) having moderate molecular weight.
  • Yang, US Pat. No. 6,316,019 discloses a process for making a tampon including the application to a substrate of a solution containing a pharmaceutically active compound.
  • the solution is liquid at a temperature of less than about 35° C, and it is applied to the disposable absorbent article at a temperature of less than 40° C.
  • US 2002/0143305 discloses a coating for substrates such as tampons that is cost efficient, provides satisfactory fluid transport and aids in removal of a tampon from an over wrapper prior to use.
  • a common theme of the art shown above is the attempt to provide a coating that is stable above room temperature, but is liquid at or near body temperature (37° C). This provides significant challenges to handling the components in high speed manufacturing processes without loss by transfer to the processing equipment.
  • Brown-Skrobot US Pat. No. 5,679,369 discloses additives to tampons to inhibit the production of toxic shock syndrome toxin-1.
  • the additives generally are not liquid at or near room temperature, and therefore, they require a carrier material, such as isopropyl alcohol. This technology represents an important advance in the art, but the disclosed process of applying the additive may require a recovery process to capture the volatile alcohol.
  • coating compositions and coated substrates that form a robust and flexible coated material and that provide desired properties to articles of manufacture used in contact with human body surfaces, such as a body-side liner or cover of an absorbent article, such as a tampon. Further, what is needed are coating compositions and coated substrates that are processable in a commercially efficient manner, that provide satisfactory fluid transport into the absorbent article, and that aid in removal of the tampon from an overwrapper or applicator prior to and/or during use.
  • coating compositions and coated substrates that form a robust and flexible coated material and that provide desired properties to articles of manufacture used in contact with human body surfaces, such as a body-side liner or cover of an absorbent article, such as a tampon.
  • coating compositions and coated substrates are processable in a commercially efficient manner, and that they provide satisfactory fluid transport into the absorbent article, and that they aid in removal of the tampon from an overwrapper or applicator prior to and/or during use.
  • a composition of matter in one embodiment, includes a flexible substrate and a coating disposed on the substrate.
  • the coating comprises 10-60 wt-% of a waxy compound and 90-40 wt-% of a diluents as described in claim 1.
  • the waxy compound is selected from the group consisting of A) monoesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said monoester has at least one hydroxyl group associated with its aliphatic alcohol residue; B) diesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said diester has at least one hydroxyl group associated with its aliphatic alcohol residue; and C) mixtures of said monoesters and diesters.
  • the coating forms a stable liquid mixture at a temperature between 35° C and 100° C, has a liquefaction temperature of at least 30° C, and has a contact angle with a flat surface of the substrate of less than 35° when measured at a temperature of 60° C.
  • the coating forms a stable liquid mixture at a temperature between 40° C and 75° C.
  • the liquid mixture has a liquefaction temperature of at least about 35° C.
  • the diluent comprises a hydrophilic agent and a lyophilic agent as described in claim 1.
  • a coating composition includes 10-60 wt-% of a waxy compound and 90-40 wt-% of a diluent as described in claim 1.
  • the waxy compound is selected from the group consisting of A) monoesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said monoester has at least one hydroxyl group associated with its aliphatic alcohol residue; B) diesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said diester has at least one hydroxyl group associated with its aliphatic alcohol residue; and C) mixtures of said monoesters and diesters.
  • the coating forms a stable liquid mixture at a temperature between 35° C and 100° C, has a liquefaction temperature of at least 30° C, and has a contact angle with a flat surface of the substrate of less than 35° when measured at a temperature of 60° C.
  • an intravaginal device in another embodiment, includes an insertable element that is substantially enclosed within a cover material.
  • the cover material includes a flexible substrate and a coating disposed on the substrate.
  • the coating includes 10-60 wt-% of a waxy compound and 90-40 wt-% of a diluent as described in claim 1.
  • the waxy compound is selected from the group consisting of A) monoesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said monoester has at least one hydroxyl group associated with its aliphatic alcohol residue; B) diesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said diester has at least one hydroxyl group associated with its aliphatic alcohol residue; and C) mixtures of said monoesters and diesters.
  • the coating forms a stable liquid mixture at a temperature between 35° C and 100° C, has a liquefaction temperature of at least 30° C, and has a contact angle with a flat surface of the substrate of less than 35° when measured at a temperature of 60° C.
  • the present invention relates to a process for adding waxy components to substrates, specifically substrates used in the manufacture of disposable absorbent articles, to the articles during manufacture, or to the finished product.
  • the process incorporates the use of a liquid solution to apply the waxy component to substrates.
  • the present invention also relates to a liquid coating composition
  • a liquid coating composition comprising the waxy component and a diluent, which liquid composition forms a stable liquid mixture at a temperature between 35° C and 100° C, has a liquefaction temperature of at least 30° C, and has a contact angle with a flat surface of the substrate of less than 35° when measured at a temperature of 60° C
  • the present invention provides is that the coated substrate is surprisingly robust. We have found that the resulting coating neither flakes off of the substrate nor is significantly rubbed off of the substrate during processing. This permits economic, high-speed processing of the coated substrate to form an article of manufacture used in contact with human body surfaces.
  • liquid is defined to be a substance that has a definite volume but no definite form except such as given by its container.
  • a solution is defined herein to be a homogeneous mixture of a substance (solid, liquid, or gas) dissolved in a liquid, the solvent.
  • surfactant refers to a surface active agent, i.e., one that modifies the nature of surfaces.
  • Surfactants are often used as wetting agents, detergents, emulsifiers, dispersing agents, penetrants, and antifoaming agents.
  • Surfactants may be anionic, cationic, nonionic and ampholytic.
  • the surfactant used in the present invention is a nonionic surfactant.
  • Nonionic surfactants are generally less irritating of human body tissue, and they are therefore more acceptable in uses that contact such tissue.
  • hydrophilic agent refers to a substance that readily associates with water
  • lyophilic agent refers to an agent that attracts lipids in a colloid system, describing a colloidal system in which the dispersed phase is a lipids and attracts the dispersing medium.
  • One measure of the relative hydrophilicity and lyophilicity of an agent is the HLB or hydrophile-lyophile balance with a high HLB reflecting a relatively hydrophilic agent and a low HLB reflecting a relatively lyophilic agent.
  • the lyophilic agents have an HLB of less than 10, more preferably, less than 8, and most preferably, less than 5.
  • the waxy compositions useful in the present invention used in the present invention are useful to inhibit the production of toxins by various bacteria as disclosed in Brown-Skrobot and Brown-Skrobot et al., U.S. Patent Nos. 5,389,374 ; 5,547,985 ; 5,641,503 ; 5,679,369 ; and 5,705,182 .
  • compositions are selected from the group consisting of: monoesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said monoester has at least one hydroxyl group associated with its aliphatic alcohol residue; diesters of a polyhydric aliphatic alcohol and a fatty acid containing from eight to eighteen carbon atoms and wherein said diester has at least one hydroxyl group associated with its aliphatic alcohol residue; and mixtures of said monoesters and diesters.
  • the active composition is glycerol monolaurate.
  • the diluents of the present invention are compatible with both the waxy composition and the substrate to which the liquid composition will be applied.
  • the diluent is a multi-component system.
  • a component diluent may be selected based upon its compatibility with the waxy component. For example, employing GML as the waxy component (HLB of 5.2, one may select diluents with a similar HLB, preferably an HLB of 5.2 +/- about 2.
  • a hydrophilic olefinic diol and optionally an additional diluent, such as a surfactant having an HLB similar to GML, e.g., about 3.2 to about 7.2, can be incorporated to form a two-component diluent.
  • an additional diluent such as a surfactant having an HLB similar to GML, e.g., about 3.2 to about 7.2, can be incorporated to form a two-component diluent.
  • the olefinic diols of the present invention are defined in claim 1 and are highly hydrophilic and/or very miscible with water.
  • aqueous bodily fluids that may be absorbed by absorbent structures treated with the present solution will have a greater affinity for such structures than for structures treated with the waxy composition of the present invention in the absence of the olefinic diol.
  • Diols of the present invention include C 2-8 diols and polyglycols.
  • the diol is selected from the group consisting of glycols (C 2 and C 3 diols) and polyglycols.
  • the term "polyglycol" refers to a dihydroxy ether formed by dehydration of two or more glycol molecules.
  • a representative, non-limiting list of useful polyglycols includes ethylene glycol, propylene glycol, polyethylene glycols, polypropylene glycols, methoxypolyethylene glycols, polybutylene glycols, or block copolymers of butylene oxide and ethylene oxide.
  • polyethylene glycol having a molecular weight of less than 600, and polypropylene glycol having a molecular weight of less than 4,000, are preferred.
  • diluents or diluent components may include surfactants, such as fatty acid esters and ethoxylated sugar derivatives.
  • Preferred fatty acid esters include sorbitan fatty acid esters.
  • a representative, non-limiting list of useful sorbitan fatty acid esters includes sorbitan monooleate (HLB: 4.3), sorbitan monostearate (HLB: 4.7), sorbitan monopalmitate (HLB: 6.7), sorbitan monolaurate (HLB: 8.6), sorbitan tristearate (HLB: 2.1), and sorbitan trioleate (HLB: 1.8).
  • sorbitan monooleate is most preferred.
  • Preferred ethoxylated sugar derivatives include the class of methyl glucose derivatives.
  • a representative, non-limiting list of useful methyl glucose derivatives includes methyl gluceth-10, methyl glucose-20, methyl glucose-20 distearate, methyl glucose dioleate (HLB: 5), and methyl glucose sesquistearate (HLB: 6), PEG-120 methyl glucose dioleate, and PEG-20 methyl glucose sesquistearate.
  • diluents or diluent components may include mono-, di-, or triglycerides that have an HLB value between 3 and 10, preferably between 3 and 7.5, including without limitation, caprylic/capric triglyceride (HLB of 5), available as NEOBEE®z® M-5 caprylic/capric triglyceride from Stephan Company Northfield, Illinois, USA; oleic triglyceride (HLB of 7), available as FLORASUNTM 90 from International Flora Technologies, Ltd, Chandler, Arizona, USA.
  • the liquid mixture includes 10 to 60 wt% of the waxy component and 90 to 40 wt-% of the diluent, more preferably 20 to 50 wt% of the waxy component and 70 to 50 wt-% of the diluent.
  • Diluent systems comprising hydrophilic and lyophilic diluent components may take the ranges shown below in Table 1: Table 1 Hydrophilic component(s) (wt-%) Lyophilic component(s) (wt-%) Useful 0-100 100-0 Preferred 25-80 75-20 More preferred 40-75 60-25 Most preferred 50-70 50-30
  • liquid composition of the present invention An example of the preparation of the liquid composition of the present invention is described below with reference to a particular system comprising glycerol monolaurate as the waxy component and a multi-component diluent system.
  • Other liquid compositions may be similarly prepared, whether there is more than one waxy component or whether there is only one diluent.
  • the diluent or diluent system will be heated to a temperature at which the waxy component(s) will be liquefied in combination with the diluent.
  • the mixture will be agitated to ensure sufficient component homogeneity, and the waxy component(s) will be added at a rate at which the liquid mixture can be maintained without solidification.
  • the liquid composition may be prepared by combining an olefinic diol and a surfactant agent while stirring and heating to about 60° C to form the diluent. While continuing to stir, the waxy substance may be added to the diluent, and the heat maintained.
  • the glycerol monolaurate may be added at a rate that does not cause the temperature of the solution to drop below 52° C. We have found that this mixture starts to clear up at ⁇ 52° C and completely clear at 55° C. Heating the solution to about 60° C can substantially assure complete mixing of the coating composition.
  • Useful substrates include, but are not limited to, films (e.g., apertured or non-apertured), fabrics (e.g., woven, knit, or non-woven), strings (e.g., threads, cords, tapes, and ribbons) and the like.
  • Films may be relatively homogenous films or may be multilayered films formed by lamination, co-extrusion, and other film-forming methods.
  • the films may be apertured to permit movement of fluids, such as gases, and more preferably liquids, through the film.
  • Fabric substrates may comprise absorbent and/or non-absorbent fibers, and the fibers may be homogeneous or multi-component.
  • a representative, non-limiting list of useful fibers includes, without limitation, cellulose, rayon, nylon, acrylic, polyester, polyethylene, polypropylene, ethylene vinyl acetate, polyurethane, and the like.
  • Multi-component fibers may be bicomponent or more and may have a sheath/core configuration, a side-by-side configuration, or other configuration that would be recognized by one of ordinary skill in the art.
  • a representative, non-limiting list of useful non-woven fabrics includes spunbonded fabric, thermal bonded fabric, resin bonded fabric, hydroentangled fabric, spun-lace fabric, meltblown fabric, needlepunched fabric, and the like; apertured and non-apertured films.
  • the coating composition may be applied to the flexible, sheet-like substrate in ways known to those of ordinary skill in the art.
  • a representative, non-limiting list of useful application methods includes dip, immersion, roller-transfer, kiss-coating, spray, doctor blade, gravure, relief print, and the like.
  • the coated substrate is rapidly chilled to form a robust flexible material.
  • the coating composition remains adhered to the substrate when substrate is bent at a 180° angle over a rod having a diameter of less than about 5 mm and does not transfer significantly to a steel surface when pressed against the surface. This is indicative that the coated substrate will stand up to the rigors of further processing to produce an article of manufacture such as a disposable absorbent article.
  • the coated substrate may be chilled through the use of a chiller device comprising an enclosure having at least an inlet to receive the coated substrate, an outlet to discharge the coated substrate, and means to cool the coated substrate and to maintain the temperature in the enclosure at a temperature of less than 0° C, more preferably to less than -20° C.
  • the amount of pharmaceutically active compound applied to a substrate is up to 4 wt-%, preferably from 0.1 to 4 weight percent; more preferably, from 0.5 to 3 weight percent; and most preferably, from 0.9 to 2.5 weight percent.
  • the amount of liquid mixture applied to the substrate, determined from the preferred solution ratios and amount of pharmaceutically active compound, is up to 10 wt-%, preferably from 0.2 to 8 weight percent; more preferably, from 1 to 6 weight percent; and most preferably, from 3 to 5 weight percent.
  • the substrates of the present invention can be used independently, or as an element in the manufacture of disposable articles.
  • Such articles can include patches for topical or transdermal applications, nasal pads (nasal tampons), diapers, incontinence products, sanitary protection products, body wipes, bedsheets and surgical gowns.
  • the substrates are elements used in the manufacture of sanitary protection and incontinence products.
  • the solutions can also be applied to finished disposable articles.
  • sanitary protection articles fall into two distinct categories, those worn externally in contact with the perineum, and those worn internally, partially or wholly contained within the vaginal canal.
  • External sanitary protection products include, without limitation, pantiliners, full-size pads, and ultrathins.
  • Internal sanitary protection products can be defined as absorbing products, such as tampons, and the like; collecting products, such as described in Contente et al., U.S. Patent Number 5,295,984 and the like; or a combination of the two.
  • U.S. Patent Numbers 4,294,253 and 4,642,108 disclose tampon constructions and processes of manufacture.
  • a preferred disposable absorbent article of the present invention, for the solution to be applied to, is a sanitary tampon.
  • Other internal products can include incontinence articles, such as pessaries and other urinary tract support devices.
  • a process for producing disposable absorbent articles comprises encasing at least a portion of an absorbent material with a liquid permeable material, wherein the discharged fluids, contact and penetrate the liquid permeable material, and are drawn into the absorbent material for storage.
  • the liquid permeable material is the coated substrate of the present invention.
  • a representative, non-limiting list of materials useful as the absorbent material includes cellulosic fibers, such as wood pulp and cotton pulp; synthetic fibers, such as polyesters and polyolefins; superabsorbent polymers, such as sodium polyacrylate, and the like.
  • the process can further comprise encasing a second portion of the absorbent material with a liquid impermeable material, to prevent the collected fluid from transferring completely through the article.
  • liquid impermeable materials include, without limitation, polymeric films or coatings, such as polyolefins (e.g., polyethylene and polypropylene), polyvinyls (e.g., polyvinyl acetate, polyvinyl chloride, and polyvinylidene chloride), copolymers (e.g., ethylene vinyl acetate), and blends or laminates of one or more of the above polymers; bodily fluid repellant structures such as nonwovens, apertured films, and repellant fiber layers integrated into the bottom layer of the absorbent materials.
  • the contact angle ( ⁇ ) is the angle at which a liquid/vapor interface meets the solid surface.
  • the contact angle is specific for any given system and is determined by the interactions across the three interfaces, LV, SV, and SL.
  • the contact angle is controlled by three forces: ⁇ LV (liquid vapor surface tension), ⁇ SV (solid vapor surface tension), and ⁇ SL (solid-liquid interfacial tension).
  • ⁇ SV liquid vapor surface tension
  • ⁇ SL solid-liquid interfacial tension
  • the contact angles in this disclosure were measured using a DSA 100 instrument (Krüss GmbH, Hamburg, Germany). Since contact angles have to be measured in molten/liquid stage, the formulations analyzed were all placed into an oven at 60° C and allowed to equilibrate, unless otherwise noted.
  • the test surfaces were created by adhering a polymer film formed of a blend of low density polyethylene, linear low density polyethylene, and high density polyethylene onto a glass substrate using double-sided tape on its sides to keep it flat. The surfaces were then placed into the sample chamber of the instrument, which was also temperature regulated at 60° C (unless otherwise noted) by a temperature-controlled water bath.
  • the samples were loaded into syringes and dispensed from a needle on to the surfaces with an approximate diameter of 0.5 mm. Drops are created and increased in size until they freely fall from the needle onto the surface. An image is captured of the drop on the surface when equilibrium is reached.
  • the contact angles are calculated by analyzing the images captured using the Drop Shape Analysis (DSA) for WindowsTM ver. 1.90.0.14 software package (Krüss GmbH, Hamburg, Germany). All of the contact angles were determined using the same fitting method to avoid variation due to the fitting method.
  • the first step is to determine the baseline, i.e. where the drop meets the surface. This can be done automatically in the software, but can be manually adjusted by one-skilled in the art.
  • the fitting method chosen was the circular segment method (circle fitting).
  • the drop outline is adapted mathematically to a circular segment shape. In this way the whole drop outline can be evaluated and not just the area of intersection with the baseline.
  • this state is characterized by the contact angle ( ⁇ ).
  • DSC Densilic Acid Determination
  • a DSC TA Instruments Model Q 200, with Universal Analysis 200 software V4.4A, Aluminum sample pans with hermetic lids
  • a formulation in liquid state is added to a pre-weighed aluminum DSC sample pan. The final sample weight was recorded and the sample pan sealed with a hermetic lid. Sample weights are in the range of 6 to 10 milligrams.
  • the DSC measurement for each sample is run a heat/cool/heat series.
  • the sample starts out at 25° C and heat is increased at a constant rate of 10 degree/min to a max of 80° C.
  • the sample is then cooled to -20° C, and reheated to 80° C with both cooling and heating rate of 10°/min.
  • the liquefaction temperature is defined and measured as the maximum of the first heat cycle or the first peak of the DSC chart.
  • tampons were produced in accordance with the general teaching of Friese et al., US Pat. No. 6,310,269 ; Leutwyler et al., US Pat. No. 5,832,576 ; PPC708; and Schoelling US Pat. App. No. 2002/0151859 employing the apertured film cover, generally as disclosed in US Pat. No. 6537414 .
  • a batch of coating formulation was prepared as follows:
  • the coating was applied to the apertured film cover material off-line prior to slitting and rolling to form an apertured film cover supply.
  • the supply (having a target amount of about 2 mg GML per tampon) was unwound on commercial processing equipment to form the tampons generally as described above. After manufacture of the tampons, the amount of GML remaining on the cover was determined by HPLC with an Evaporative Light Scattering Detector.
  • a series of coating compositions was prepared, generally as follows:
  • DSC MP was measured from the first solid to liquid heat absorption peak.
  • Contact Angle is the contact angle of a formulation at 60° C on a flat PE film placing on a 60° C surface
  • SPAN® 80 is sorbitan monooleate with HLB value of 4.3
  • Neobee® M-5 is a caprylic triglyceride with HLB value of 5
  • FlorasunTM 90 is an oleic triglyceride with HLB value of 7

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Claims (9)

  1. Beschichtungszusammensetzung umfassend:
    a) etwa 10-60 Gew.-% einer wachsartigen Verbindung aus der Gruppe bestehend aus:
    i) Monoestern eines mehrwertigen aliphatischen Alkohols und einer Fettsäure mit acht bis achtzehn Kohlenstoffatomen, wobei der Monoester mindestens eine mit seinem aliphatischen Alkoholrest assoziierte Hydroxylgruppe aufweist;
    ii) Diestern eines mehrwertigen aliphatischen Alkohols und einer Fettsäure mit acht bis achtzehn Kohlenstoffatomen, wobei der Diester mindestens eine mit seinem aliphatischen Alkoholrest assoziierte Hydroxylgruppe aufweist;
    iii) Mischungen der Monoester und Diester; und
    b) etwa 90-40 Gew.-% eines Verdünnungsmittels, umfassend:
    i) ein hydrophiles Mittel aus der Gruppe bestehend aus C2-8-Diolen und Polyglykolen und
    ii) ein lyophiles Mittel mit einem HLB-Wert von weniger als 10;
    wobei die Beschichtung bei einer Temperatur zwischen 35°C und 100°C eine stabile flüssige Mischung bildet, eine Verflüssigungstemperatur von mindestens 30° C aufweist und einen Kontaktwinkel mit einer flachen Oberfläche des Substrats von weniger als 35° bei Messung einer Temperatur von 60°C aufweist.
  2. Zusammensetzung nach Anspruch 1, wobei die Beschichtung bei einer Temperatur zwischen 40°C und 75°C eine stabile flüssige Mischung bildet.
  3. Zusammensetzung nach Anspruch 1, wobei die flüssige Mischung eine Verflüssigungstemperatur von mindestens 35°C aufweist.
  4. Zusammensetzung nach Anspruch 1, wobei das hydrophile Mittel ein olefinisches Diol umfasst.
  5. Stoffzusammensetzung, umfassend:
    a) ein flexibles Substrat;
    b) eine auf dem Substrat angeordnete Beschichtung, wobei die Beschichtung eine Zusammensetzung nach einem der Ansprüche 1 bis 4 umfasst.
  6. Intravaginale Vorrichtung, umfassend:
    a) ein insertierbares Element;
    b) weitgehend umschlossen mit einem Abdeckmaterial, umfassend die Stoffzusammensetzung nach Anspruch 5.
  7. Intravaginale Vorrichtung nach Anspruch 6, wobei das flexible Substrat einen Film umfasst.
  8. Intravaginale Vorrichtung nach Anspruch 7, wobei der Film einen Film mit Öffnungen umfasst.
  9. Intravaginale Vorrichtung nach Anspruch 6, wobei das flexible Substrat einen Vliesstoff umfasst.
EP09828206.4A 2008-11-21 2009-11-19 Beschichtungszusammensetzungen und beschichtete substrate für fertigungsartikel, die in kontakt mit flächen des menschlichen körpers verwendet werden Active EP2367682B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL09828206T PL2367682T3 (pl) 2008-11-21 2009-11-19 Kompozycje powlekające i powleczone podkłady w wyrobach stosowanych w kontakcie z powierzchniami ciała człowieka

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11678508P 2008-11-21 2008-11-21
PCT/US2009/065110 WO2010059800A1 (en) 2008-11-21 2009-11-19 Coating compositions and coated substrates for articles of manufacture used in contact with human body surfaces

Publications (3)

Publication Number Publication Date
EP2367682A1 EP2367682A1 (de) 2011-09-28
EP2367682A4 EP2367682A4 (de) 2013-04-24
EP2367682B1 true EP2367682B1 (de) 2014-04-16

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EP09828206.4A Active EP2367682B1 (de) 2008-11-21 2009-11-19 Beschichtungszusammensetzungen und beschichtete substrate für fertigungsartikel, die in kontakt mit flächen des menschlichen körpers verwendet werden

Country Status (10)

Country Link
US (1) US8237011B2 (de)
EP (1) EP2367682B1 (de)
JP (1) JP5575788B2 (de)
CN (1) CN102209626B (de)
AU (1) AU2009316605B2 (de)
BR (1) BRPI0921382B8 (de)
CA (1) CA2741852C (de)
PL (1) PL2367682T3 (de)
RU (1) RU2528258C2 (de)
WO (1) WO2010059800A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002318018A1 (en) * 2001-07-19 2003-03-03 Peter James Brian Lamb A tampon
EP2720862B1 (de) 2011-06-17 2016-08-24 Fiberweb, Inc. Dampfdurchlässiger und im wesentlichen wasserundurchlässiger mehrschichtiger artikel
WO2012178027A2 (en) 2011-06-23 2012-12-27 Fiberweb, Inc. Vapor-permeable, substantially water-impermeable multilayer article
US9827755B2 (en) 2011-06-23 2017-11-28 Fiberweb, Llc Vapor-permeable, substantially water-impermeable multilayer article
EP2723567A4 (de) 2011-06-24 2014-12-24 Fiberweb Inc Dampfdurchlässiger und im wesentlichen wasserundurchlässiger mehrschichtiger artikel
AU2013249086A1 (en) * 2012-04-20 2014-10-30 Hennepin Life Sciences Compositions for topical treatment of microbial infections
JP2022190895A (ja) * 2021-06-15 2022-12-27 住友ゴム工業株式会社 タイヤ及びタイヤと車両との組合せ体

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3796219A (en) 1971-03-24 1974-03-12 Kimberly Clark Co Coated tampon
DE2855179C2 (de) 1978-12-20 1982-06-09 Dr. Carl Hahn GmbH, 4000 Düsseldorf Tampon für die Frauenhygiene
US4438167A (en) 1979-10-15 1984-03-20 Biax Fiberfilm Corporation Novel porous fabric
DE3204124A1 (de) * 1982-02-06 1983-08-18 Bayer Ag, 5090 Leverkusen Antimykotische tampons mit hoher wirkstoff-freisetzung
DE3236540A1 (de) 1982-10-02 1984-04-05 Henkel KGaA, 4000 Düsseldorf Tampon fuer die frauenhygiene und verfahren zu dessen herstellung
US5641503A (en) 1989-04-27 1997-06-24 Mcneil-Ppc, Inc. Additives to tampons
DE3934153A1 (de) 1989-10-12 1991-04-18 Johnson & Johnson Gmbh Tampon, insbesondere fuer die frauenhygiene, sowie verfahren und vorrichtung zur herstellung desselben
US5295984A (en) 1989-12-07 1994-03-22 Ultrafem, Inc. Vaginal discharge collection device and intravaginal drug delivery system
NZ250714A (en) 1990-10-30 1996-05-28 Mcneil Ppc Inc Liquid composition comprising esters of higher fatty acids for use as a vaginal douche and to prevent toxic shock toxin production
NZ264247A (en) 1990-10-30 1996-07-26 Mcneil Ppc Inc Absorbent product containing mono- or diesters of a polyhydric alcohol and a c8-18 fatty acid having at least one free hydroxyl group in sufficient amount to inhibit the production of enterotoxins a, b and c by staph. aureus
DE4304505C2 (de) 1993-02-15 1995-05-18 Johnson & Johnson Gmbh Tampon, insbesondere für die Frauenhygiene, sowie Verfahren und Vorrichtung zur Herstellung desselben
US5466685A (en) 1993-05-13 1995-11-14 Johnson & Johnson Inhibition of expression of beta-lactamase using esters of fatty acid alcohols
US6433246B1 (en) 1995-12-22 2002-08-13 Mcneil-Ppc, Inc. Tampon having improved early expansion characteristics
US6096332A (en) * 1998-06-30 2000-08-01 Mcneil-Ppc, Inc. Adding pharmaceutically active compounds to substrates
US6762339B1 (en) * 1999-05-21 2004-07-13 3M Innovative Properties Company Hydrophilic polypropylene fibers having antimicrobial activity
US6537414B1 (en) 1999-06-30 2003-03-25 Hans-Werner Schoelling Sealing roller and sealing roller element particularly for producing a tampon for feminine hygiene and method therefor
US6570055B2 (en) 2000-12-21 2003-05-27 Mcneil-Ppc, Inc Apertured polymeric film web with surfactant mixture additive
DE10114786C2 (de) 2001-03-26 2003-07-17 Johnson & Johnson Gmbh Tampon für die Frauenhygiene sowie Verfahren und Vorrichtung zur Herstellung desselben
DE10300506A1 (de) * 2003-01-08 2004-07-22 Cognis Deutschland Gmbh & Co. Kg Wachsdispersionen

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CA2741852A1 (en) 2010-05-27
AU2009316605A1 (en) 2010-05-27
JP5575788B2 (ja) 2014-08-20
WO2010059800A1 (en) 2010-05-27
US8237011B2 (en) 2012-08-07
CN102209626B (zh) 2014-07-09
EP2367682A1 (de) 2011-09-28
AU2009316605B2 (en) 2014-01-30
RU2011125318A (ru) 2012-12-27
US20100130951A1 (en) 2010-05-27
RU2528258C2 (ru) 2014-09-10
BRPI0921382A2 (pt) 2015-12-29
JP2012509711A (ja) 2012-04-26
CN102209626A (zh) 2011-10-05
CA2741852C (en) 2016-10-11
BRPI0921382B1 (pt) 2021-04-06
PL2367682T3 (pl) 2014-09-30
EP2367682A4 (de) 2013-04-24
BRPI0921382B8 (pt) 2021-05-25

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